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Synthesis, characterization, and bioactivities of copper complexes with N-substituted Di(picolyl)amines

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Abstract

Three new Cu(II) complexes with ethyl bis(2-pyridylmethyl)amino-2-propionate (Etdpa), or bis(2-pyridylmethyl)amino-2-propionate (Adpa), were synthesized and characterized by physico-chemical and spectroscopic methods. The X-ray crystal structure of [(Adpa)CuCl] shows that the copper(II) atom is coordinated by three N atoms, one oxygen atom from the ligand (Adpa) and one chloride anion, forming a trigonal bipyramidal geometry. The spectrophotometric and fluorescence titration data indicate that the interaction of square pyramidal [(Etdpa)CuCl2] with ct-DNA is weak, but the trigonal bipyramidal complexes [(Adpa)Cu(H2O)](ClO4) and [(Adpa)CuCl] interact with ct-DNA with the mode of intercalation. The inhibition activities of the three new copper(II) complexes on the four cancer cells (Mcf-7, Eca-109, A549, and Hela) are in the order: [(Adpa)Cu(H2O)](ClO4) > [(Adpa)CuCl] > [(Etdpa)CuCl2], which correlates with their DNA-binding properties. The results show that the substituents introduced on the secondary amino nitrogen atom of dpa have great contribution to the antitumor activities of these copper(II) complexes. It is also found that the coordination of copper(II) ions with AdpaH can decrease the toxicity of AdpaH.

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Acknowledgements

Financial support from National Science Foundation of China (20777029B0702), distinguished scholar science foundation of Jiangsu University (06JDG050), and the foundation of state key Laboratory of Coordination Chemistry, Nanjing University.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangsu University, 212013, Zhenjiang, People’s Republic of China

    Lin-Yun Wang, Qiu-Yun Chen, Juan Huang & Kun Wang

  2. College of Pharmacy MSC09 5360, 1 University of New Mexico, Albuquerque, NM, 87131-0001, USA

    Chang-Jian Feng

  3. State Key Laboratory of Coordination Chemistry, Nanjing University, 212093, Nanjing, People’s Republic of China

    Zhi-Rong Gen

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  1. Lin-Yun Wang
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Correspondence to Qiu-Yun Chen.

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Supplementary material 1 (DOC 831 kb)

Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 691109 for 3. The data can be obtained free of charge via http://www.ccdc.cam.ac.uk, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk.

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Wang, LY., Chen, QY., Huang, J. et al. Synthesis, characterization, and bioactivities of copper complexes with N-substituted Di(picolyl)amines. Transition Met Chem 34, 337–345 (2009). https://doi.org/10.1007/s11243-009-9200-5

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